Poly(ethylene glycol)-b/ock-poly(acrylic acid-co-acrylamidophenylboronic acid) [PEG(114)-b-(PAA(63)-co-PAAPBA(107))] was synthesized by the modification of poly(ethylene glycol)-block-poly(acrylic acid) (PEG(114)-b-PAA(170)) with 3-aminophenyl-boronic acid (APBA). Glucose-responsive PEG(114)-b-(PAA(63)-co-PAAPBA(107)) self-assembled into core-shell micelles with the hydrophobic core composed of PAAPBA and hydrophilic shell composed of PEG in aqueous solution. The swelling and disaggregating behaviors of micelles responding to glucose were investigated by using light scattering in aqueous solution at pH 7.4. Characterization of insulin-loaded micelles and their drug release in solutions with various glucose concentrations were further studied. The results demonstrated that the drug release rate can be controlled by variation of glucose concentration.